Hydrochloric Acid → 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 2206850Notes

Reaction equation

HRID 2206850 reaction equation
[F:1][CH:2]([F:13])[C:3]1[C:7]([C:8](F)=[O:9])=[C:6]([F:11])[N:5]([CH3:12])[N:4]=1.[OH-:14].[Na+].Cl>S1(=O)(=O)CCCC1>[F:11][C:6]1[N:5]([CH3:12])[N:4]=[C:3]([CH:2]([F:13])[F:1])[C:7]=1[C:8]([OH:14])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 585266223-(Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl fluoride

Product 1

HCID 231925843-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

67.5 g of a solution (10% molar) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl fluoride in tetrahydrothiophene-1,1-dioxide were added dropwise to 400 mL of an aqueous 1N NaOH solution. During the addition, the temperature was kept below 20° C. After 2 h of stirring at room temperature, the mixture was carefully acidified to pH 2 using concentrated hydrochloric acid. The white precipitate formed was filtered off, washed with water and dried. This gave 6 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white solid.

Workup

  1. additionDuring the addition
  2. customwas kept below 20° C
  3. customThe white precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8631682824a4469686579bd9731578c9
Source dataset
uspto-grants-2016_06
Patent number
US09375004B2

Reaction notes

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